TW576832B - Quinolinecarboxylic acid derivative or salts thereof - Google Patents

Quinolinecarboxylic acid derivative or salts thereof Download PDF

Info

Publication number: TW576832B
Authority: TW; Taiwan
Prior art keywords: compound; acid; salt; salts; reaction
Prior art date: 1999-07-01

Application number

TW089112608A

Other languages

English (en)

Chinese (zh)

Inventor

Akira Yazaki

Yoshiko Niino

Yasuhiro Kuramoto

Yuzo Hirao

Yoshihiro Oshita

Original Assignee

Wakunaga Pharma Co Ltd

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1999-07-01

Filing date

2000-06-27

Publication date

2004-02-21

2000-06-27 Application filed by Wakunaga Pharma Co Ltd filed Critical Wakunaga Pharma Co Ltd

2004-02-21 Application granted granted Critical

2004-02-21 Publication of TW576832B publication Critical patent/TW576832B/zh

Links

150000003839 salts Chemical class 0.000 title claims abstract description 36
LOAUVZALPPNFOQ-UHFFFAOYSA-N quinaldic acid Chemical class C1=CC=CC2=NC(C(=O)O)=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-N 0.000 title description 3
150000001875 compounds Chemical class 0.000 claims abstract description 58
230000000844 anti-bacterial effect Effects 0.000 claims abstract description 17
-1 6-amino-3,5-difluoropyridine-2-yl Chemical group 0.000 claims description 27
239000002253 acid Substances 0.000 claims description 13
239000004480 active ingredient Substances 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims description 2
239000008194 pharmaceutical composition Substances 0.000 claims 2
JVLFMTZUPSBCNJ-UHFFFAOYSA-N 3,5-difluoropyridin-2-amine Chemical compound NC1=NC=C(F)C=C1F JVLFMTZUPSBCNJ-UHFFFAOYSA-N 0.000 claims 1
210000004369 blood Anatomy 0.000 abstract description 6
239000008280 blood Substances 0.000 abstract description 6
239000003814 drug Substances 0.000 abstract description 5
208000035473 Communicable disease Diseases 0.000 abstract description 4
241001465754 Metazoa Species 0.000 abstract description 2
231100000053 low toxicity Toxicity 0.000 abstract description 2
230000003449 preventive effect Effects 0.000 abstract description 2
KUPIYDHNVRWZKK-UHFFFAOYSA-N 1-(6-amino-3,5-difluoropyridin-2-yl)-8-bromo-7-[3-(ethylamino)azetidin-1-yl]-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C1C(NCC)CN1C1=C(F)C=C2C(=O)C(C(O)=O)=CN(C=3C(=CC(F)=C(N)N=3)F)C2=C1Br KUPIYDHNVRWZKK-UHFFFAOYSA-N 0.000 abstract 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 31
229940125904 compound 1 Drugs 0.000 description 26
238000006243 chemical reaction Methods 0.000 description 23
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
239000002904 solvent Substances 0.000 description 14
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
230000000694 effects Effects 0.000 description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
238000000034 method Methods 0.000 description 9
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
230000000052 comparative effect Effects 0.000 description 8
239000007787 solid Substances 0.000 description 8
238000012360 testing method Methods 0.000 description 8
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
229910052757 nitrogen Inorganic materials 0.000 description 7
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
206010034972 Photosensitivity reaction Diseases 0.000 description 6
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 description 6
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 6
208000007578 phototoxic dermatitis Diseases 0.000 description 6
231100000018 phototoxicity Toxicity 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
150000001298 alcohols Chemical class 0.000 description 5
239000003242 anti bacterial agent Substances 0.000 description 5
150000007514 bases Chemical class 0.000 description 5
239000003795 chemical substances by application Substances 0.000 description 5
229940125782 compound 2 Drugs 0.000 description 5
125000005843 halogen group Chemical group 0.000 description 5
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239000000203 mixture Substances 0.000 description 5
239000000843 powder Substances 0.000 description 5
238000002360 preparation method Methods 0.000 description 5
239000000243 solution Substances 0.000 description 5
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DCTOHCCUXLBQMS-UHFFFAOYSA-N 1-undecene Chemical compound CCCCCCCCCC=C DCTOHCCUXLBQMS-UHFFFAOYSA-N 0.000 description 4
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
150000001241 acetals Chemical class 0.000 description 4
HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 description 4
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
150000002170 ethers Chemical class 0.000 description 4
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
239000002798 polar solvent Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 4
239000008096 xylene Substances 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical class N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
241000894006 Bacteria Species 0.000 description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
206010015150 Erythema Diseases 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
208000010201 Exanthema Diseases 0.000 description 3
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
230000005856 abnormality Effects 0.000 description 3
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 3
125000000217 alkyl group Chemical group 0.000 description 3
125000003277 amino group Chemical group 0.000 description 3
239000002585 base Substances 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
230000036772 blood pressure Effects 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
238000002512 chemotherapy Methods 0.000 description 3
MYSWGUAQZAJSOK-UHFFFAOYSA-N ciprofloxacin Chemical compound C12=CC(N3CCNCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 MYSWGUAQZAJSOK-UHFFFAOYSA-N 0.000 description 3
239000003085 diluting agent Substances 0.000 description 3
239000012153 distilled water Substances 0.000 description 3
231100000321 erythema Toxicity 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
201000005884 exanthem Diseases 0.000 description 3
230000029142 excretion Effects 0.000 description 3
238000001727 in vivo Methods 0.000 description 3
238000002955 isolation Methods 0.000 description 3
239000011976 maleic acid Substances 0.000 description 3
150000007522 mineralic acids Chemical class 0.000 description 3
125000004433 nitrogen atom Chemical group N* 0.000 description 3
238000007254 oxidation reaction Methods 0.000 description 3
229910000027 potassium carbonate Inorganic materials 0.000 description 3
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 3
229930185107 quinolinone Natural products 0.000 description 3
206010037844 rash Diseases 0.000 description 3
230000035484 reaction time Effects 0.000 description 3
229910000029 sodium carbonate Inorganic materials 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
210000002700 urine Anatomy 0.000 description 3
HZONRRHNQILCNO-UHFFFAOYSA-N 1-methyl-2h-pyridine Chemical compound CN1CC=CC=C1 HZONRRHNQILCNO-UHFFFAOYSA-N 0.000 description 2
PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 2
238000005160 1H NMR spectroscopy Methods 0.000 description 2
HGUFODBRKLSHSI-UHFFFAOYSA-N 2,3,7,8-tetrachloro-dibenzo-p-dioxin Chemical compound O1C2=CC(Cl)=C(Cl)C=C2OC2=C1C=C(Cl)C(Cl)=C2 HGUFODBRKLSHSI-UHFFFAOYSA-N 0.000 description 2
VVAKEQGKZNKUSU-UHFFFAOYSA-N 2,3-dimethylaniline Chemical compound CC1=CC=CC(N)=C1C VVAKEQGKZNKUSU-UHFFFAOYSA-N 0.000 description 2
JEBJIWLJHQOTIA-UHFFFAOYSA-N 2-hydroxy-4-quinolone-3-carboxylic acid Chemical compound C1=CC=C2NC(=O)C(C(=O)O)=C(O)C2=C1 JEBJIWLJHQOTIA-UHFFFAOYSA-N 0.000 description 2
YSLIPUSJNFIFAB-UHFFFAOYSA-N 2-oxopyridine-1-carboxylic acid Chemical class OC(=O)N1C=CC=CC1=O YSLIPUSJNFIFAB-UHFFFAOYSA-N 0.000 description 2
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
244000063299 Bacillus subtilis Species 0.000 description 2
235000014469 Bacillus subtilis Nutrition 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
241000282472 Canis lupus familiaris Species 0.000 description 2
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 2
238000005481 NMR spectroscopy Methods 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
229920002472 Starch Polymers 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
150000001340 alkali metals Chemical class 0.000 description 2
229910000147 aluminium phosphate Inorganic materials 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
125000004429 atom Chemical group 0.000 description 2
230000001580 bacterial effect Effects 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
150000001639 boron compounds Chemical class 0.000 description 2
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
239000002775 capsule Substances 0.000 description 2
150000001735 carboxylic acids Chemical class 0.000 description 2
238000007796 conventional method Methods 0.000 description 2
238000001816 cooling Methods 0.000 description 2
PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 2
229940079593 drug Drugs 0.000 description 2
210000005069 ears Anatomy 0.000 description 2
239000003995 emulsifying agent Substances 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
238000001914 filtration Methods 0.000 description 2
NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical group C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
235000019253 formic acid Nutrition 0.000 description 2
239000001530 fumaric acid Substances 0.000 description 2
239000007789 gas Substances 0.000 description 2
150000008282 halocarbons Chemical class 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
230000031891 intestinal absorption Effects 0.000 description 2
239000007788 liquid Substances 0.000 description 2
239000001656 lutein Substances 0.000 description 2
229960005375 lutein Drugs 0.000 description 2
ORAKUVXRZWMARG-WZLJTJAWSA-N lutein Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CCCC1(C)C)C=CC=C(/C)C=CC2C(=CC(O)CC2(C)C)C ORAKUVXRZWMARG-WZLJTJAWSA-N 0.000 description 2
235000012680 lutein Nutrition 0.000 description 2
229910052749 magnesium Inorganic materials 0.000 description 2
239000011777 magnesium Substances 0.000 description 2
230000002503 metabolic effect Effects 0.000 description 2
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
150000002905 orthoesters Chemical class 0.000 description 2
239000006187 pill Substances 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
239000011591 potassium Substances 0.000 description 2
NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
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MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 2
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UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
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229910052708 sodium Inorganic materials 0.000 description 2
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RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
OGYGFBZFWNMNHB-UHFFFAOYSA-N 1,4-dimethylcyclohexa-2,4-diene-1-sulfonic acid Chemical compound CC1=CCC(C)(S(O)(=O)=O)C=C1 OGYGFBZFWNMNHB-UHFFFAOYSA-N 0.000 description 1
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HDIJZFORGDBEKL-UHFFFAOYSA-N 2,3,4-trimethylbenzoic acid Chemical compound CC1=CC=C(C(O)=O)C(C)=C1C HDIJZFORGDBEKL-UHFFFAOYSA-N 0.000 description 1
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ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
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WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
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WIKDURKPSJEWGB-UHFFFAOYSA-N phenylmethoxymethanedithioic acid Chemical compound SC(=S)OCC1=CC=CC=C1 WIKDURKPSJEWGB-UHFFFAOYSA-N 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
239000011698 potassium fluoride Substances 0.000 description 1
235000003270 potassium fluoride Nutrition 0.000 description 1
NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
229910000105 potassium hydride Inorganic materials 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
230000002265 prevention Effects 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
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YNCMLFHHXWETLD-UHFFFAOYSA-N pyocyanin Chemical compound CN1C2=CC=CC=C2N=C2C1=CC=CC2=O YNCMLFHHXWETLD-UHFFFAOYSA-N 0.000 description 1
MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
238000012552 review Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
231100000046 skin rash Toxicity 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
239000011775 sodium fluoride Substances 0.000 description 1
235000013024 sodium fluoride Nutrition 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
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239000008117 stearic acid Substances 0.000 description 1
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BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
239000013589 supplement Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
QENJZWZWAWWESF-UHFFFAOYSA-N tri-methylbenzoic acid Natural products CC1=CC(C)=C(C(O)=O)C=C1C QENJZWZWAWWESF-UHFFFAOYSA-N 0.000 description 1
YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
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239000000080 wetting agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4709—Non-condensed quinolines and containing further heterocyclic rings
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Communicable Diseases (AREA)
Immunology (AREA)
Oncology (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Pain & Pain Management (AREA)
Rheumatology (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Urology & Nephrology (AREA)
Epidemiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

TW089112608A 1999-07-01 2000-06-27 Quinolinecarboxylic acid derivative or salts thereof TW576832B (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP18749299		1999-07-01

Publications (1)

Publication Number	Publication Date
TW576832B true TW576832B (en)	2004-02-21

Family

ID=16207019

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
TW089112608A TW576832B (en)	1999-07-01	2000-06-27	Quinolinecarboxylic acid derivative or salts thereof

Country Status (25)

Country	Link
US (1)	US6858625B1 (de)
EP (1)	EP1193266B1 (de)
JP (1)	JP3477465B2 (de)
KR (1)	KR100628414B1 (de)
CN (1)	CN1157389C (de)
AT (1)	ATE248162T1 (de)
AU (1)	AU766014B2 (de)
BR (1)	BR0012192A (de)
CA (1)	CA2376760C (de)
CZ (1)	CZ302033B6 (de)
DE (1)	DE60004846T2 (de)
DK (1)	DK1193266T3 (de)
ES (1)	ES2206257T3 (de)
HK (1)	HK1047103B (de)
HU (1)	HUP0201549A3 (de)
IL (2)	IL147043A0 (de)
MX (1)	MXPA02000103A (de)
NO (1)	NO321803B1 (de)
NZ (1)	NZ516201A (de)
PT (1)	PT1193266E (de)
RU (1)	RU2236408C2 (de)
SK (1)	SK285814B6 (de)
TW (1)	TW576832B (de)
WO (1)	WO2001002390A1 (de)
ZA (1)	ZA200110357B (de)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2001017991A1 (en) *	1999-09-02	2001-03-15	Wakunaga Pharmaceutical Co., Ltd.	Quinolinecarboxylic acid derivative or its salt
US7172535B2 (en) *	2004-10-28	2007-02-06	Volmar John F	Upper back exercise machine and method of use
JP3995705B2 (ja) *	2004-11-17	2007-10-24	湧永製薬株式会社	新規ピリドンカルボン酸誘導体又はその塩
PL3766876T3 (pl) *	2008-09-24	2024-04-02	Melinta Subsidiary Corp.	Preparat farmaceutyczny zawierający pochodną chinolonu

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2548664B1 (fr) *	1983-07-06	1986-03-21	Provesan Sa	Derives 7-(pyrrol-l-yl) des acides l-ethyl-1,4-dihydro-4-oxoquinoleine-3-carboxyliques et l-ethyl-1,4-dihydro-4-oxo-(1,8-naphtyridine)-3-carboxyliques substitues, leur preparation et leur application en tant que medicaments
NO177302C (no)	1989-03-16	1995-08-23	Esteve Labor Dr	Analogifremgangsmåte til fremstilling av terapeutisk aktive substituerte azetidinylkinolon(naftyridon)karboksylsyrederivater
EP0713487B1 (de) *	1993-08-13	2000-04-19	Dong Wha Pharmaceutical Industrial Co. Ltd.	Neue chinoloncarbonsäurederivate
EP0787720B1 (de) *	1994-10-20	2003-07-16	Wakunaga Seiyaku Kabushiki Kaisha	Pyridoncarboxylat- derivate oder salze davon und antibakterielle zusammensetzungen die diese als aktiven bestandteil enthalten
DK0992501T3 (da) *	1995-09-22	2002-10-28	Wakunaga Pharma Co Ltd	Pyridoncarboxylsyre derivater som antibakterielle midler
PT897919E (pt) *	1996-04-19	2004-11-30	Wakunaga Pharma Co Ltd	Novos derivados do acido piridonacarboxilico ou seus sais e agentes anti-bacterianos contendo-os como ingrediente activo
US6136823A (en) *	1996-11-28	2000-10-24	Wakunaga Pharmaceutical Co., Ltd.	Pyridonecarboxylic acid derivatives or salts thereof and drugs containing the same as the active ingredient
DE19652239A1 (de) *	1996-12-16	1998-06-18	Bayer Ag	Verwendung von 7-(2-Oxa-5,8-diazabicyclo[4.3.0]non-8-yl)-chinolon- und -naphthyridoncarbonsäure-Derivaten zur Therapie von Helicobacter-pylori-Infektionen und den damit assoziierten gastroduodenalen Erkrankungen
JPH11292873A (ja)	1998-04-07	1999-10-26	Dainippon Pharmaceut Co Ltd	キノロンカルボン酸誘導体の製造方法およびその中間体

2000
- 2000-06-22 MX MXPA02000103A patent/MXPA02000103A/es active IP Right Grant
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- 2000-06-22 WO PCT/JP2000/004096 patent/WO2001002390A1/ja not_active Ceased
- 2000-06-22 EP EP00940804A patent/EP1193266B1/de not_active Expired - Lifetime
- 2000-06-22 RU RU2002102491/04A patent/RU2236408C2/ru not_active IP Right Cessation
- 2000-06-22 CN CNB008095884A patent/CN1157389C/zh not_active Expired - Fee Related
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- 2000-06-22 KR KR1020017016021A patent/KR100628414B1/ko not_active Expired - Fee Related
- 2000-06-22 PT PT00940804T patent/PT1193266E/pt unknown
- 2000-06-22 HU HU0201549A patent/HUP0201549A3/hu unknown
- 2000-06-22 DE DE60004846T patent/DE60004846T2/de not_active Expired - Lifetime
- 2000-06-22 SK SK1916-2001A patent/SK285814B6/sk not_active IP Right Cessation
- 2000-06-22 ES ES00940804T patent/ES2206257T3/es not_active Expired - Lifetime
- 2000-06-22 BR BR0012192-4A patent/BR0012192A/pt not_active Application Discontinuation
- 2000-06-22 US US10/019,436 patent/US6858625B1/en not_active Expired - Fee Related
- 2000-06-22 DK DK00940804T patent/DK1193266T3/da active
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- 2000-06-22 CZ CZ20014598A patent/CZ302033B6/cs not_active IP Right Cessation
- 2000-06-22 IL IL14704300A patent/IL147043A0/xx active IP Right Grant
- 2000-06-27 TW TW089112608A patent/TW576832B/zh not_active IP Right Cessation
2001
- 2001-12-12 IL IL147043A patent/IL147043A/en not_active IP Right Cessation
- 2001-12-18 ZA ZA200110357A patent/ZA200110357B/en unknown
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Also Published As

Publication number	Publication date
KR20020020733A (ko)	2002-03-15
NO20016378L (no)	2002-02-28
CA2376760A1 (en)	2001-01-11
RU2236408C2 (ru)	2004-09-20
AU5567900A (en)	2001-01-22
KR100628414B1 (ko)	2006-09-26
US6858625B1 (en)	2005-02-22
CN1358183A (zh)	2002-07-10
AU766014B2 (en)	2003-10-09
HUP0201549A3 (en)	2003-11-28
ZA200110357B (en)	2002-12-18
ATE248162T1 (de)	2003-09-15
ES2206257T3 (es)	2004-05-16
EP1193266A4 (de)	2002-08-14
EP1193266A1 (de)	2002-04-03
HK1047103B (zh)	2005-04-08
NO321803B1 (no)	2006-07-03
HUP0201549A2 (en)	2002-08-28
JP3477465B2 (ja)	2003-12-10
CZ20014598A3 (cs)	2002-05-15
DE60004846T2 (de)	2004-06-03
IL147043A0 (en)	2002-08-14
NO20016378D0 (no)	2001-12-27
WO2001002390A1 (en)	2001-01-11
BR0012192A (pt)	2002-06-18
CZ302033B6 (cs)	2010-09-08
NZ516201A (en)	2003-06-30
MXPA02000103A (es)	2003-07-21
EP1193266B1 (de)	2003-08-27
DK1193266T3 (da)	2003-11-24
SK285814B6 (sk)	2007-08-02
CA2376760C (en)	2008-11-25
HK1047103A1 (en)	2003-02-07
DE60004846D1 (de)	2003-10-02
PT1193266E (pt)	2003-12-31
CN1157389C (zh)	2004-07-14
SK19162001A3 (sk)	2002-06-04
IL147043A (en)	2007-07-04

Legal Events

Date	Code	Title	Description
2012-11-21	MM4A	Annulment or lapse of patent due to non-payment of fees

Publication	Publication Date	Title
RU2177945C1 (ru)	2002-01-10	Производное пиридонкарбоновой кислоты или его соль
JP2742248B2 (ja)	1998-04-22	７−（４−アミノメチル−３−オキシム）ピロリジン置換体を持つ新規なキノリンカルボン酸誘導体およびその製造方法
FI77855C (fi)	1989-05-10	Foerfarande foer framstaellning av terapeutiskt anvaendbara 6-fluor-1,4-dihydro-4-oxo-3- kinolinkarboxylsyraderivat.
EP0132845A2 (de)	1985-02-13	1,8-Naphthyridinderivate und Verfahren zu ihrer Herstellung
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IE912801A1 (en)	1992-02-12	Novel tricyclic compound or salts thereof, method for¹producing the same and antimicrobial agent containing the¹same
JPH0653741B2 (ja)	1994-07-20	６，７―二置換された１―シクロプロピル―１，４―ジヒドロ―４―オキソ―１，８―ナフチリジン―３―カルボン酸類
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JPH0725873A (ja)	1995-01-27	キノロン誘導体又はその塩並びに該化合物を含有する抗菌剤
JPH05255319A (ja)	1993-10-05	新規キノロン誘導体又はその塩、並びに該化合物を含有する抗菌剤
JPH0649060A (ja)	1994-02-22	５−アミノ−７−（５−アザスピロ〔２，４〕ヘプタン−５−イル）キノリン−３−カルボン酸誘導体